Blog platforms seem to be split on the issue. For example, Tumblr posts are frequently in the form blogname.com/post/967129380, which is less understandable than something like blogname.com/2010/08/post_title employed by some (all?) Moveable Type blogs.

Is this something that an average user cares about, or is it a waste of time to carefully design each URL? (It's probably obvious to avoid using URLs like app.com/index.aspx?u=1235-08236.236,d41d8cd00b2427e:a25, but how obsessive do I need to be?)

In this case, we care less about the date, but rather which blog the post resided under.
Since we've hired one of the best SEO experts in the country to re-arrange our URLs, I can definitely say it's the right way to go (not necessarily this exact format, but something friendly that represents the way your site and information is arranged).

Also, more and more people are sharing pages they like on FB, LinkedIn, Twitter, etc., so your URL gets much more exposure than it used to.

"Since we've hired one of the best SEO experts in the country to re-arrange our URLs, I can definitely say it's the right way to go" seems like reverse reasoning: it's good because he says it is, rather than it's good because it works?
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Rahul♦Aug 17 '10 at 21:51

Good point :) It also worked and multiplied our pageviews many times over :)
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Dan BarakAug 18 '10 at 4:28

Conversely, If you run the type of site where you don't want a user to be able to "hack" the url, you may not want to use a user-friendly format. You can configure your security to prevent user's from accessing the directories, but if you use an easy-to-guess schema a user might be able to get to your content just by guessing.
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LoganGoesPlacesAug 17 '10 at 17:39

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@LoganGoesPlaces - if you are using URL "hiding" as your method of content security, you really aren't creating a secure system. You system should be looking up (in the back-end) whether or not a specific user has access to a specific piece of content and then throwing an error or warning message if that user does not have access to the content.
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Charles BoyungAug 17 '10 at 18:43

I agree completely, but that only works if they are accessing a web page. If they are accessing the file directly ('hacking' the url), there is no script to check to make sure they have permission. And not everyone has access to IIS settings etc.
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LoganGoesPlacesAug 17 '10 at 19:16

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@LoganGoesPlaces - you sure CAN make sure that every file is checked by your security code, and it rarely requires IIS settings. Trust me, I've done it on several different occasions and it really isn't that hard to do, especially in modern platforms. And while we're at it, if you need to have access to IIS to do something for security's sake, and you don't have access to IIS, then you should change your hosting so you CAN do that. URL "hiding" is absolutely useless as a security mechanism. Just ask ANY security expert.
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Charles BoyungAug 17 '10 at 19:33

I would be interested in knowing how you check that. It must be something running on the server that is doing the authentication as opposed to the website itself. Regardless of that, if you use an easy to guess structure, anyone can plug in a few file name guesses and gain access to non-public files. I know because I have done it.
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LoganGoesPlacesAug 17 '10 at 19:52

You're right that most users probably aren't going to notice the URL. That said, why make things deliberately sloppy? More advanced users will appreciate the care you put into readable/hackable URLs and, as Sruly pointed out, it helps a ton with SEO.

I think it is very important in some cases, like user pages or something that people might want to share in say a forum signature.. really anything where a person might want to present the url as content and have it be understood.